The other day, while standing in front of the mirror, I realized something scary.

My criteria for success has changed. I used to ask myself whether I looked good. Now I ask myself whether I don’t look too bad.

I’m not sure exactly when this changed but it did. 

I changed my focus from “winning” to “not losing”.

Where I was once driven to work out, eat right, sleep well, etc., now I am satisfied if I just avoid things that are bad for me. Those few extra pounds that prevented me looking good, aren’t as troublesome as they once were, since they don’t make me look that bad. I’ve lowered the bar. It’s not surprising that my weight continues to increase. 

You can slip pretty far from good before you are actually “bad”.

As leaders, we need to create a culture of people who strive to win rather than than just avoiding losing.

I first learned this lesson as a high school wrestler.  It was only my second year wrestling but I had been put on the varsity team (needless to say, I lost a lot). My opponent was a senior ranked third in the state. With 30 seconds left in the match, we were tied. There was a pause in the match. I went back to my corner and my coach said something I’ll never forget, “You still have time to beat him.”

I tried to pin my opponent. He easily countered and escaped earning one point. He won the match.

I sulked back to my corner expecting to get chewed out by my coach. But instead he said, “Good job.” I reminded him that I had just lost. He replied, “I didn’t expected you to win. I expected you to try to win.”

A loss while trying to win was far better than settling for a tie.

That moment changed my view. Had he not empowered me to take a risk or had he penalized me for not staying the course and accepting a tie, I would have had a very different, and average, wrestling career (not that mine was all that outstanding but it was certainly better than average).

Looking back on my business career, my time as a high school wrestler has even more meaning. The times that I’ve failed have been when I was trying not to lose – the safe opinion that wouldn’t stir controversy, the easy project that I could deliver with my eyes closed, or those times when I tried to stay below the radar. My successes have come when I tried to win -doing those things that other people thought not possible or going after the high visibility projects.

The same thing happens in the business with whom I work. Organizations, teams, and individuals try not to lose rather than strive to win. The result is cautious decision making, risk aversion, and only doing things that have been “tried and true”. Over time, these organizations go from being good to not bad to irrelevant. The very actions they take to avoid losing are the ones that, in the end, drive their loss.

Leaders who encourage their people to play it safe (whether implicitly or explicitly) create cultures of people who play not to lose. They hit their targets and meet their deadlines but never create the “killer app” or innovative idea. Their departments don’t detract from the business but aren’t seen as value creators or essential functions. At best, they generate indifference from the rest of the business.

It’s time to start playing to win. Encourage your people to take chances. Allow them to swing for the fence and understand that they might strike out more. In the end, you’ll win more games and have more impact.